In 1963, Allan Sherman hit number one on Billboard with “My Son, the Nut,” and it was the last comedy album to top the charts. Until now. “Weird Al” Yankovic’s 14th studio album, “Mandatory Fun,” landed at number one this week, selling 104,000 copies, according to Nielsen SoundScan. Cynics would be quick to point out that an album largely based on parodying recent pop songs like Lorde’s “Royals” and Pharrell Williams’ “Happy” demonstrates the sad state of the music industry, but Yankovic’s cultivated a rabid fanbase over the last 30 years. His “Mandatory Fun” roll-out plan capitalized on that last week, when he released eight videos in eight consecutive days, each becoming its own viral hit. The biggest so far has been his song “Word Crimes,” a parody of Robin Thicke’s smash single “Blurred Lines,” that laments terrible grammar – its garnered more than 10 million views to date. (He also premiered one video, “Mission Statement,” here on Speakeasy.)

Speakeasy talked with Yankovic about his rise to the top of the charts, song parodies in the Internet age and why he flew to Colorado just for rapper Iggy Azalea’s approval.

The last time a comedian had the number one album in the country, it was 1963 – you were just three years old. Why did “Mandatory Fun” break this streak?

“Mandatory Fun” is my best album to date and I think the marketing campaign had a lot to do with it. The “eight videos in eight days” seem to resonate extremely well with the online community. That had a snowball effect as well. I took advantage of the viral nature of the Internet and gave people something to be excited about.

Does hitting number one make any broader statements about the music industry in your eyes?

What it means as far as the recording industry or the zeitgeist, I’ll let somebody else figure that out.

With the Internet giving a voice to every amateur “Weird Al” with a phone and a YouTube account, has writing hits become harder?

The mechanics of writing my songs haven’t changed all that much. But perhaps the perception has changed. For the first couple decades of my career, I had the field virtually to myself. But now with the advent of portals like YouTube, there are tens of thousands doing funny videos of song parodies and I never again will be the only person that has done a parody of any given pop song. I just know now that the marketplace is crowded, I’m not the only game in town. I guess if anything, it’s forced me to step up my game and not go with the most obvious idea.

In looking at songs to parody, do you think of how viral the originals were? Or are you just a big Iggy Azalea fan?

When I do parodies, I try to structure them so that people can appreciate them even if they’re not familiar with the original source material. But having said that, obviously I try to produce songs that are very popular – songs that have hopefully reached the top of the Billboard charts. There’s also other little parameters that would make it more a target. If the song has a very identifiable lyric or hook, has some kind of characteristics that are easy to lampoon – those are all pluses. But usually it just boils down to finding a popular song that I can come up with a half-way clever idea from.

Pop stars largely stay the same age as you get older. Do you ever feel like you’re chasing youth?

[Laughs.] Well, I’ve been doing this for a long time. The fact that a 54-year-old guy just got the number one album on Billboard is pretty amazing as well. I don’t feel old. I try not to act old. A lot of people don’t perceive me as being my present age. Doing this thing that you love keeps you young. I don’t know if I’m going to be doing this in my 90s. I’m guessing not.

Your song “Word Crimes” laments bad grammar. Does it really drive you crazy?

It does. But I want to be careful here because I’ve been taken to task for writing a song that encourages bullying of people with poor grammar. That’s not my intention. There’s a bit of me in “Word Crimes” the same way there’s a bit of me in [2006’s] “White and Nerdy.” I drew a lot of that song from personal experience. It stems from my distaste for bad grammar but it’s also a parody of the kind of prescriptivists that would lose their minds over grammar infractions.

Now when you make parodies, it must be a badge of honor for the original artists. Did you hear from Pharrell, Iggy or Lorde?

Normally I don’t talk to the artists but I actually did contact Pharrell and Iggy in person. Pharrell through email – he was extremely nice and said he was honored to have the parody. I talked to Iggy in person, which was out of necessity because we needed an answer from her. We weren’t getting our phone calls returned from her management. So I flew out to Denver just so I could bump into her as she was getting off stage, which I did. I introduced myself and handed her the lyrics to my song and said “We’re hoping to be recording this tomorrow in Los Angeles, I want to make sure you’re okay with it. She scanned the lyrics and said “Seems okay.” I said “Thank you very much” and I went and got back on a plane.

The lengths you go for these.

The thing is I don’t necessarily need to get permission at all, but historically I’ve always thought that was the right thing to do, because I respect artists and don’t want to burn bridges. I think one of the reasons I’ve been able to hang around in the industry as long as I have, is because I do want to respect the artists and make sure they feel like they’re in on the joke.

What’s your accordion collection like these days?

I’ve got about five or six. A couple in storage for the tour, one in Hawaii and two here in L.A. They’re scattered around.

How is Weird Al going to celebrate his first number one record?

I think I’m going to have a burrito.

“Mandatory Fun” is out now on RCA Records. Stream it via Spotify below:

About Speakeasy

Speakeasy is a blog covering media, entertainment, celebrity and the arts. The publication is produced by Barbara Chai and Jonathan Welsh with contributions from the Wall Street Journal staff and others. Write to us at speakeasy@wsj.com or follow us on Twitter at @WSJSpeakeasy or individually @barbarachai.